16669-99-1

Usage

InChI:InChI=1/C16H12O4/c17-13-4-2-1-3-12(13)14(18)7-5-11-6-8-15-16(9-11)20-10-19-15/h1-9,17H,10H2

Upstream product

• 120-57-0 piperonal 
• 118-93-4 o-hydroxyacetophenone 
• 261785-32-4 3-(o-acetoxyphenyl)-1-(3',4'-methylenedioxyphenyl)prop-2-yn-ol 
• 2620-47-5 1-(benzo[d][1,3]dioxol-5-yl)prop-2-yn-1-ol 
• 32865-61-5 2-iodophenyl acetate 
• 582-24-1 1-phenyl-2-hydroxyethanone 

Downstream Products

• 54401-45-5 2-(benzo[d][1,3]dioxol-5-yl)-4H-chromen-4-one 
• 109255-62-1 (4-benzo[1,3]dioxol-5-yl-3,4-dihydro-2H-pyrazol-3-yl)-(2-hydroxy-phenyl)-ketone 
• 56202-04-1 1-(2-hydroxyphenyl)-3-(3,4-methylenedioxyphenyl)propanone 
• 36685-58-2 3',4'-methylenedioxyaurone 
• 54401-46-6 2-(benzo[d][1,3]dioxol-5-yl)chroman-4-one 
• 36136-89-7 3-(3,4-methylenedioxy-phenyl)-4-chromone 
• 2373-80-0 3,4-methylenedioxy-trans-cinnamic acid 
• 873934-69-1 2-[2-(benzo[d][1,3]dioxol-5-yl)-2,3-dihydrobenzo-[b][1,4]thiazepin-4-yl]phenol 

Relevant academic research and scientific papers

SAR Studies and Biological Characterization of a Chromen-4-one Derivative as an Anti- Trypanosoma brucei Agent

Chemical modulation of the flavonol 2-(benzo[d][1,3]dioxol-5-yl)-chromen-4-one (1), a promising anti-Trypanosomatid agent previously identified, was evaluated through a phenotypic screening approach. Herein, we have performed structure-activity relationsh

3-substituted propyl-2-alkene-1-ketone compound and application thereof

The invention relates to the technical field of medicine and particularly discloses a 3-substituted propyl-2-alkene-1-ketone compound and application thereof to preparation of antifungal drugs and synergistic antifungal drugs. The compound can be used tog

The synthesis and synergistic antifungal effects of chalcones against drug resistant Candida albicans

To identify effective and low toxicity synergistic antifungal compounds, 24 derivatives of chalcone were synthesized to restore the effectiveness of fluconazole against fluconazole-resistant Candida albicans. The minimal inhibitory concentration (MIC80) and the fractional inhibitory concentration index (FICI) of the antifungal synergist fluconazole were measured against fluconazole-resistant Candida albicans. This was done via methods established by the clinical and laboratory standards institute (CLSI). Of the synthesized compounds, 2′-hydroxy-4′-methoxychalcone (8) exhibited the most potent in vitro (FICI = 0.007) effects. The structure activity relationship of the compounds are then discussed.

Scaffold-hopping of bioactive flavonoids: Discovery of aryl-pyridopyrimidinones as potent anticancer agents that inhibit catalytic role of topoisomerase IIα

A strategy of scaffold-hopping of bioactive natural products, flavones and isoflavones, leading to target-based discovery of potent anticancer agents has been reported for the first time. Scaffold-hopped flavones, 2-aryl-4H-pyrido[1,2-a]pyrimidin-4-ones and the scaffold-hopped isoflavones, 3-aryl-pyrido[1,2-a]pyrimidin-4-ones were synthesized via Pd-catalyzed activation–arylation methods. Most of the compounds were found to exhibit pronounced human topoisomerase IIα (hTopoIIα) inhibitory activities and several compounds were found to be more potent than etoposide (a hTopoIIα-inhibiting anticancer drug). These classes of compounds were found to be hTopoIIα-selective catalytic inhibitors while not interfering with topoisomerase I and interacted with DNA plausibly in groove domain. Cytotoxicities against various cancer cells, low toxicity in normal cells, and apoptotic effects were observed. Interestingly, compared to parent flavones/isoflavones, their scaffold-hopped analogs bearing alike functionalities showed significant/enhanced hTopoIIα-inhibitory and cytotoxic properties, indicating the importance of a natural product-based scaffold-hopping strategy in the drug discovery.

QSAR, in silico docking and in vitro evaluation of chalcone derivatives as potential inhibitors for H1N1 virus neuraminidase

Thirty three chalcones were synthesized and tested on viral H1N1 neuraminidase activity by using MUNANA assay [2′-(4-methylumbelliferyl)-α-d-N-acetylneuraminic acid] assay with DANA (2,3-didehydro-2-deoxy-N-acetylneuraminic acid) was used as standard. 2D and 3D-quantitative structure?activity relationship models have been successfully developed with a good correlative and predictive ability for quantitative structure?activity relationships of these chalcone derivatives. Result from the 2D-quantitative structure?activity relationship model indicates that electrostatic parameter enhanced bioactivity of the chalcones while steric substituents diminished their potency as H1N1 neuraminidase inhibitors. 3D-quantitative structure?activity relationship model showed the importance of the position of the hydroxyl group in chalcone derivatives which can influence on hydrophobicity, hydrogen bond donor and aromatic ring features that enhance the biological activity. Finally, docking studies showed that chalcones MC8 and MC16 with low C docker interaction energies and higher numbers of hydrogen bonding have better inhibitory activity against viral H1N1 neuraminidase.

Discovery of 2′-hydroxychalcones as autophagy inducer in A549 lung cancer cells

A series of 2′-hydroxychalcone derivatives was synthesized and the effects of all the compounds on growth of A549 lung cancer cell were investigated. The results showed that all compounds had inhibitory effects on the growth of A549 lung cancer cells and compound 2-7 possessed the highest growth inhibitory effect and induced autophagy of A549 lung cancer cells.

Chalcones with electron-withdrawing and electron-donating substituents: Anticancer activity against TRAIL resistant cancer cells, structure-activity relationship analysis and regulation of apoptotic proteins

In the present study, a series of 46 chalcones were synthesised and evaluated for antiproliferative activities against the human TRAIL-resistant breast (MCF-7, MDA-MB-231), cervical (HeLa), ovarian (Caov-3), lung (A549), liver (HepG2), colorectal (HT-29), nasopharyngeal (CNE-1), erythromyeloblastoid (K-562) and T-lymphoblastoid (CEM-SS) cancer cells. The chalcone 38 containing an amino (-NH2) group on ring A was the most potent and selective against cancer cells. The effects of the chalcone 38 on regulation of 43 apoptosis-related markers in HT-29 cells were determined. The results showed that 20 apoptotic markers (Bad, Bax, Bcl-2, Bcl-w, Bid, Bim, CD40, Fas, HSP27, IGF-1, IGFBP-4, IGFBP-5, Livin, p21, Survivin, sTNF-R2, TRAIL-R2, XIAP, caspase-3 and caspase-8) were either up regulated or down regulated.

Dual inhibition of the α-glucosidase and butyrylcholinesterase studied by Molecular Field Topology Analysis

A striking dual inhibition of enzymes α-glucosidase and butyrylcholinesterase by small drug-like molecules, including 1,4-disubstituted-1,2,3-triazoles, chalcones, and benzothiazepines, was rationalized with the help of Molecular Field Topology Analysis, a 3D QSAR technique similar to CoMFA. A common pharmacophore supported the concept of a link existing between type-2 diabetes mellitus and Alzheimer's disease. These findings will be instrumental for rational design of drug candidates for both of these conditions.

COMPOSITION FOR TREATING DIABETES AND METABOLIC DISEASES AND A PREPARATION METHOD THEREOF

Disclosed is a chalcone composition for treating diabetes and metabolic syndromes. In particular, the chalcone compound bound with 2-halogen in ring A significantly decreases the blood glucose level in the in vitro anti-diabetic effect experiment. In the in vivo animal model, the leading chalcone compound can prevent the progression of diabetes and control the blood glucose level, and there is no significant difference in the gains in body weight. Throughout the seven-week administration, there are no hepatic or renal toxicity observed.

Biological and structure-activity evaluation of chalcone derivatives against bacteria and fungi

The present work describes the antibacterial and antifungal activities of several chalcones obtained by a straight Claisen-Schmidt aldol condensation determined by the minimal inhibitory concentration against different microorganisms (Gram-positive and Gram-negative bacteria and fungi). Solid state crystal structures of seven chalcones were determined by X-ray diffraction (XRD) analysis. Chemometric studies were carried out in order to identify a potential structureactivity relationship.